메뉴 건너뛰기




Volumn 26, Issue 2, 2007, Pages 181-188

An alternative advantageous protocol for efficient synthesis of phosphorothioate oligonucleotides utilizing phenylacetyl disulfide (PADS)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; DISULFIDE; OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; PHENYLACETYL DISULFIDE; PYRIDINE; REAGENT; UNCLASSIFIED DRUG;

EID: 33847057669     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770601112739     Document Type: Article
Times cited : (5)

References (26)
  • 1
    • 0026606239 scopus 로고
    • Advances in the synthesis of oligonucleotides by the phosphoramidite Approach
    • (a) Beaucage, S.L.; Iyer, R.P. Advances in the synthesis of oligonucleotides by the phosphoramidite Approach. Tetrahedron 1992, 48, 2223-2311;
    • (1992) Tetrahedron , vol.48 , pp. 2223-2311
    • Beaucage, S.L.1    Iyer, R.P.2
  • 2
    • 0027469581 scopus 로고
    • Phosphoramidite derivatives and their synthetic applications
    • (b) Beaucage, S.L.; Iyer, R.P. Phosphoramidite derivatives and their synthetic applications. Tetrahedron 1993, 49, 1925-1963;
    • (1993) Tetrahedron , vol.49 , pp. 1925-1963
    • Beaucage, S.L.1    Iyer, R.P.2
  • 3
    • 33847059470 scopus 로고    scopus 로고
    • Beaucage, S.L. Oligonucleotide Synthesis. In Comprehensive Natural Product Chemistry, Barton, D.H.R., Nakanishi, K., eds., Pergamon Press, New York, 1999; 7.05, p. 105.
    • (c) Beaucage, S.L. Oligonucleotide Synthesis. In Comprehensive Natural Product Chemistry, Barton, D.H.R., Nakanishi, K., eds., Pergamon Press, New York, 1999; vol. 7.05, p. 105.
  • 4
    • 0037708617 scopus 로고    scopus 로고
    • Ravikumar, V.T.; Kumar, R.K.; Capaldi, D.C.; Turney, B.; Rentel, C.; Cole, D.L. Antisense phosphorothioate oligodeoxyribonucleotide targeted against ICAM-1: Use of I-linker to eliminate 3′-terminal phosphorothioate monoester formation. Org. Proc. Res. Dev. 2003, 7, 259-266 and references cited therein;
    • (a) Ravikumar, V.T.; Kumar, R.K.; Capaldi, D.C.; Turney, B.; Rentel, C.; Cole, D.L. Antisense phosphorothioate oligodeoxyribonucleotide targeted against ICAM-1: Use of I-linker to eliminate 3′-terminal phosphorothioate monoester formation. Org. Proc. Res. Dev. 2003, 7, 259-266 and references cited therein;
  • 6
    • 0005915514 scopus 로고    scopus 로고
    • Recent development in scale up of modified oligodeoxynucleotides
    • and references cited therein
    • (c) Zhang, Z.; Tang, J-Y. Recent development in scale up of modified oligodeoxynucleotides. Current Op. Drug Disc. Develop. 1998, 1, 304-313 and references cited therein.
    • (1998) Current Op. Drug Disc. Develop , vol.1 , pp. 304-313
    • Zhang, Z.1    Tang, J.-Y.2
  • 7
    • 0347379925 scopus 로고    scopus 로고
    • Human RNase H1 uses one tryptophan and two lysines to position the enzyme at the 3′-DNA/5′-RNA terminus of the heteroduplex substrate
    • (a) Lima, W.F.; Wu, H.; Nichols, J.G.; Prakash, T.P.; Ravikumar, V.; Crooke, S.T. Human RNase H1 uses one tryptophan and two lysines to position the enzyme at the 3′-DNA/5′-RNA terminus of the heteroduplex substrate. J. Biol. Chem. 2003, 278, 49860-49867;
    • (2003) J. Biol. Chem , vol.278 , pp. 49860-49867
    • Lima, W.F.1    Wu, H.2    Nichols, J.G.3    Prakash, T.P.4    Ravikumar, V.5    Crooke, S.T.6
  • 8
    • 0031278019 scopus 로고    scopus 로고
    • Perspectives in antisense therapeutics
    • (b) Agrawal, S.; Iyer, R.P. Perspectives in antisense therapeutics. Pharmacol. Ther. 1997, 76, 151-160;
    • (1997) Pharmacol. Ther , vol.76 , pp. 151-160
    • Agrawal, S.1    Iyer, R.P.2
  • 9
    • 0000015743 scopus 로고    scopus 로고
    • Antisense oligonucleotides: Basic concepts and mechanisms
    • (c) Dias, N.; Stein, C.A. Antisense oligonucleotides: Basic concepts and mechanisms. Mol. Cancer Ther. 2002, 1, 347-355;
    • (2002) Mol. Cancer Ther , vol.1 , pp. 347-355
    • Dias, N.1    Stein, C.A.2
  • 10
    • 0035992697 scopus 로고    scopus 로고
    • Efficiency of antisense oligonucleotide drug discovery
    • (d) Bennett, C.F. Efficiency of antisense oligonucleotide drug discovery. Antisense Nucleic Acid Drug Dev. 2002, 12, 215-224.
    • (2002) Antisense Nucleic Acid Drug Dev , vol.12 , pp. 215-224
    • Bennett, C.F.1
  • 12
    • 33847057177 scopus 로고    scopus 로고
    • A number of second-generation phosphorothioate oligonucleotides are in various stages of preclinical and clinical trials against APOB-100, PTP-1B, VLA4, TRPM2, survivin, STAT-3. eIF-4E, etc. for the treatment of a variety of diseases such as cancer, psoriasis, diabetes, asthma, arthritis, multiple sclerosis, etc
    • A number of second-generation phosphorothioate oligonucleotides are in various stages of preclinical and clinical trials against APOB-100, PTP-1B, VLA4, TRPM2, survivin, STAT-3. eIF-4E, etc. for the treatment of a variety of diseases such as cancer, psoriasis, diabetes, asthma, arthritis, multiple sclerosis, etc.
  • 13
    • 0038833714 scopus 로고    scopus 로고
    • Suska, A.; Grajkowski, A.; Wilk, A.; Uznanski, B.; Blaszczyk, J.; Wieczorek, M.; Stec, W.J. Antisense oligonucleotides: Stereocontrolled synthesis of phosphorothioate oligonucleotides. Pure & Appl. Chem. 1993, 4, 707-714 and references cited therein;
    • (a) Suska, A.; Grajkowski, A.; Wilk, A.; Uznanski, B.; Blaszczyk, J.; Wieczorek, M.; Stec, W.J. Antisense oligonucleotides: Stereocontrolled synthesis of phosphorothioate oligonucleotides. Pure & Appl. Chem. 1993, 4, 707-714 and references cited therein;
  • 14
    • 33748216395 scopus 로고    scopus 로고
    • Stec, W.J.; Wilk, A. Stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s. Angew. Chem. Int. Ed. Engl. 1994, 33, 709-722 and references cited therein;
    • (b) Stec, W.J.; Wilk, A. Stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s. Angew. Chem. Int. Ed. Engl. 1994, 33, 709-722 and references cited therein;
  • 15
    • 0027263477 scopus 로고
    • Stereocontrolled synthesis of P-chiral analogues of oligonucleotides
    • (c) Lesnikowski, Z.J. Stereocontrolled synthesis of P-chiral analogues of oligonucleotides. Bioorg. Chem. 1993, 21, 127-155.
    • (1993) Bioorg. Chem , vol.21 , pp. 127-155
    • Lesnikowski, Z.J.1
  • 17
    • 0038110909 scopus 로고    scopus 로고
    • Solid phase synthesis of phosphorothioate oligonucleotides utilizing diethyldithiocarbonate disulfide (DDD) as an efficient sulfur transfer reagent
    • and references cited therein
    • (a) Cheruvallath, Z.S.; Kumar, R.K.; Rentel, C.; Cole, D.L.; Ravikumar, V.T. Solid phase synthesis of phosphorothioate oligonucleotides utilizing diethyldithiocarbonate disulfide (DDD) as an efficient sulfur transfer reagent. Nucleosides Nucleotides & Nucleic Acids 2003, 22, 461-468 and references cited therein.
    • (2003) Nucleosides Nucleotides & Nucleic Acids , vol.22 , pp. 461-468
    • Cheruvallath, Z.S.1    Kumar, R.K.2    Rentel, C.3    Cole, D.L.4    Ravikumar, V.T.5
  • 18
    • 0034385487 scopus 로고    scopus 로고
    • Synthesis of antisense oligonucleotides: Replacement of 3 H-1,2-benzodithiol-3-one 1,1-dioxide (Beaucage reagent) with phenylacetyl disulfide (PADS) as efficient sulfurization reagent: From bench to bulk manufacture of active pharmaceutical ingredient
    • (a) Cheruvallath, Z.S.; Carty, R.L.; Moore, M.N.; Capaldi, D.C.; Krotz, A.H.; Wheeler, P.D.; Turney, B.J.; Craig, S.R.; Gaus, H.J.; Scozzari, A.N.; Cole, D.L.; Ravikumar, V.T. Synthesis of antisense oligonucleotides: Replacement of 3 H-1,2-benzodithiol-3-one 1,1-dioxide (Beaucage reagent) with phenylacetyl disulfide (PADS) as efficient sulfurization reagent: From bench to bulk manufacture of active pharmaceutical ingredient. Org. Proc. Res. Dev. 2000, 4, 199-204;
    • (2000) Org. Proc. Res. Dev , vol.4 , pp. 199-204
    • Cheruvallath, Z.S.1    Carty, R.L.2    Moore, M.N.3    Capaldi, D.C.4    Krotz, A.H.5    Wheeler, P.D.6    Turney, B.J.7    Craig, S.R.8    Gaus, H.J.9    Scozzari, A.N.10    Cole, D.L.11    Ravikumar, V.T.12
  • 19
    • 10044246137 scopus 로고    scopus 로고
    • Phosphorothioate oligonucleotides with low phosphate diester content: Greater than 99.9% sulfurization efficiency with "aged" solutions of phenylacetyl disulfide (PADS)
    • (b) Krotz, A.H.; Gorman, D.; Mataruse, P.; Foster, C.; Godbout, J.D.; Coffin, C.C.; Scozzari, A.N. Phosphorothioate oligonucleotides with low phosphate diester content: Greater than 99.9% sulfurization efficiency with "aged" solutions of phenylacetyl disulfide (PADS). Org. Proc. Res. Dev. 2004, 8, 852-858;
    • (2004) Org. Proc. Res. Dev , vol.8 , pp. 852-858
    • Krotz, A.H.1    Gorman, D.2    Mataruse, P.3    Foster, C.4    Godbout, J.D.5    Coffin, C.C.6    Scozzari, A.N.7
  • 20
    • 84987209605 scopus 로고
    • A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates
    • (c) Roelen, H.C.P.F.; Kamer, P.C.J.; van den Eist, H.; van der Marel, G.A.; van Boom, J.H. A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates. Recl. Trav. Chim. Pays-Bas 1991, 110, 325-331;
    • (1991) Recl. Trav. Chim. Pays-Bas , vol.110 , pp. 325-331
    • Roelen, H.C.P.F.1    Kamer, P.C.J.2    van den Eist, H.3    van der Marel, G.A.4    van Boom, J.H.5
  • 21
  • 22
    • 0025250111 scopus 로고
    • 3 H-1,2-Benzodithiole-3-one 1,1-dioxide as an improved sulfuring reagent in the solid phase synthesis of oligodeoxyribonucleoside phosphorothioates
    • (a) Iyer, R.P.; Egan, W.; Regan, J.B.; Beaucage, S.L. 3 H-1,2-Benzodithiole-3-one 1,1-dioxide as an improved sulfuring reagent in the solid phase synthesis of oligodeoxyribonucleoside phosphorothioates. J. Am. Chem. Soc. 1990, 112, 1253-1254;
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 1253-1254
    • Iyer, R.P.1    Egan, W.2    Regan, J.B.3    Beaucage, S.L.4
  • 23
    • 0025161168 scopus 로고
    • The automated synthesis of sulfur-containing oligodeoxyribonucleotides using 3 H-1,2-benzodithiol-3-one 1,1-dioxide as a sulfur-transfer reagent
    • (b) Iyer, R.P.; Phillips, L.R.; Egan, W.; Regan, J.B.; Beaucage, S.L. The automated synthesis of sulfur-containing oligodeoxyribonucleotides using 3 H-1,2-benzodithiol-3-one 1,1-dioxide as a sulfur-transfer reagent. J. Org. Chem. 1990, 55, 4693-4699.
    • (1990) J. Org. Chem , vol.55 , pp. 4693-4699
    • Iyer, R.P.1    Phillips, L.R.2    Egan, W.3    Regan, J.B.4    Beaucage, S.L.5
  • 24
    • 0033484252 scopus 로고    scopus 로고
    • Is it essential to use anhydrous acetonitrile in the manufacture of phosphorothioate oligonucleotides
    • (a) Capaldi, D.C.; Scozzari, A.N.; Cole, D.L.; Ravikumar, V.T. Is it essential to use anhydrous acetonitrile in the manufacture of phosphorothioate oligonucleotides. Org. Process Res. Dev. 1999, 3, 485-487;
    • (1999) Org. Process Res. Dev , vol.3 , pp. 485-487
    • Capaldi, D.C.1    Scozzari, A.N.2    Cole, D.L.3    Ravikumar, V.T.4
  • 25
    • 0035886957 scopus 로고    scopus 로고
    • Effect of molecular sieves in the liquid-phase synthesis of nucleotide via the phosphoramidite method
    • (b) Hayakawa, Y.; Hirata, A.; Sugimoto, J.; Kawai, R.; Sakakura, A.; Kataoka, M. Effect of molecular sieves in the liquid-phase synthesis of nucleotide via the phosphoramidite method. Tetrahedron 2001, 57, 8823-8826.
    • (2001) Tetrahedron , vol.57 , pp. 8823-8826
    • Hayakawa, Y.1    Hirata, A.2    Sugimoto, J.3    Kawai, R.4    Sakakura, A.5    Kataoka, M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.